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Structure of 204905-77-1

Chemical Structure| 204905-77-1

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Product Details of [ 204905-77-1 ]

CAS No. :204905-77-1
Formula : C7H6O3S
M.W : 170.18
SMILES Code : O=CC1=C2C(OCCO2)=CS1
MDL No. :MFCD01651766
InChI Key :GNVXYRDVJKJZTO-UHFFFAOYSA-N
Pubchem ID :3540090

Safety of [ 204905-77-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 204905-77-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 5
Fraction Csp3 0.29
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 40.58
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

63.77 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.72
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.11
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.33
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.17
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.0
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.4

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.86
Solubility 2.32 mg/ml ; 0.0137 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.04
Solubility 1.54 mg/ml ; 0.00907 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.64
Solubility 3.89 mg/ml ; 0.0229 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.55 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.81

Application In Synthesis of [ 204905-77-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 204905-77-1 ]

[ 204905-77-1 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 68-12-2 ]
  • [ 126213-50-1 ]
  • [ 211235-87-9 ]
  • [ 204905-77-1 ]
  • 2
  • [ 4546-04-7 ]
  • [ 204905-77-1 ]
  • 2,2'-(3,4-ethylenedioxy)dithienyl-ω,ω'-1,4-divinyl benzene [ No CAS ]
  • 3
  • [ 71702-74-4 ]
  • [ 204905-77-1 ]
  • 2,2'-(3,4-ethylenedioxythienyl)-ω,ω'-2,5-divinylthiophene [ No CAS ]
  • 4
  • [ 68-12-2 ]
  • [ 126213-50-1 ]
  • [ 204905-77-1 ]
YieldReaction ConditionsOperation in experiment
86.3% With bis(trichloromethyl) carbonate; In dichloromethane; at 0 - 35℃; for 1h; To a mixture of EDOT (15.0 g, 0.1 mol) and DMF (11.0 g, 0.15 mol), BTC (11.9 g, 0.04 mol) dissolved in dry CH2Cl2 (80 mL) was added dropwise at 0C. The mixture was heated to 35C and stirred for 1 h, then cooled and poured into ice water (250 mL). The pH of the aqueous phase was adjusted to 7-8 with 10% sodium hydroxide and the organic phase was separated. The aqueous phase was extracted with CH2Cl2 for three times. The organic phase was combined and dried with anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the crude product was recrystallized in 95% ethanol to yield white needle crystals 1 (15.5 g, 86.3% yield). 1H NMR (400 MHz) delta/ppm: 9.90 (s, 1H), 6.79 (s, 1H), 4.38-4.25 (m, 4H).
83% With trichlorophosphate; at -10 - 20℃; for 4h;Cooling with ice; 3,4-Ethylenedioxythiophene (2 mL, 18 mmol) was dissolved in dry N N-Dimethylformamide(DMF) (10 mL, 126 mmol), the mixture was cooled to -10 C and POCl3 (1.76 mL, 18 mmol)was added slowly dropwise over min. The reaction mixture was then allowed to reach roomtemperature then stirred for an additional hour. The reaction was poured into an ice bath andneutralized using a basic aqueous solution. The product, in the form of white needles, wasfiltered and dried, yielding a quantitative yield (3.06 g). 1H NMR (300 MHz, CDCl3 , deltappm ):9.83 (s, 1H), 6.74 (s, 1H), 4.31 (d, 2H), 4.21 (d, 2H). 13C NMR (75 MHz, CDCl3 , deltappm ):180.0, 141.7, 110.8, 110.7, 65.2, 64.3.
67% With trichlorophosphate; at 0 - 20℃; for 8h;Inert atmosphere; 5g (35.21 mmol) of 3,4-ethylenedioxythiophene was dissolved in 70 mL of N,N-dimethylformamide (DMF) in a two-necked flask, magnetically stirred and argon gas was introduced, the reaction system was lowered to 0 C, and 10.8 g (70.42 mmol) of phosphorus oxychloride was added dropwise to the system, and the reaction system was slowly returned to room temperature for 8 h overnight. After the reaction is completed, a rotary evaporator was used to spin dried DMF, the system was reduced to 0 C, 50 mL of saturated sodium bicarbonate solution was added to quench the excess phosphorus oxychloride, extracted and separated with 3*50 mL of dichloromethane and organic phase was spin dried, the sample was mixed with silica gel, and 4g of product was obtained by column chromatography, yield was 67%. The structure of the intermediate is resolved as follows:
  • 5
  • [ 34904-03-5 ]
  • [ 204905-77-1 ]
  • 2-[(Z)-(4-N,N-dimethylaminobenzylidene)methyl]-3,4-ethylenedioxythiophene [ No CAS ]
  • 2-[(E)-(4-N,N-dimethylaminobenzylidene)methyl]-3,4-ethylenedioxythiophene [ No CAS ]
  • 6
  • [ 20893-30-5 ]
  • [ 204905-77-1 ]
  • 1-cyano-2-(2-(3,4-ethylenedioxythienyl))-1-(2-thienyl)vinylene [ No CAS ]
  • 7
  • [ 204905-77-1 ]
  • [ 204905-81-7 ]
  • 1-cyano-1,2-bis(2-(3,4-ethylenedioxythienyl))vinylene [ No CAS ]
  • 8
  • [ 101737-73-9 ]
  • [ 204905-77-1 ]
  • 1,4-bis[1-cyano-2-{3,4-(ethylenedioxy)thien-2-yl}vinyl]-2,5-dibutoxybenzene [ No CAS ]
  • 9
  • [ 204905-77-1 ]
  • [ 852054-42-3 ]
YieldReaction ConditionsOperation in experiment
91% With N-Bromosuccinimide; In acetonitrile; at 0 - 20℃; for 60h;Inert atmosphere; Compound 1 (4.04 g, 23.7 mmol) was suspended in dry acetonitrile (100 mL) and cooled to0 C. NBS (4.36 g, 26.0 mmol), 1.1 equiv, was added and the mixture was stirred for 60 h atroom temperature, shielded from light and under nitrogen. The color changed from yellow topurple. The mixture was transferred with 150 mL of ethyl acetate to a separation funnel,washed with 10% aqueous Na2CO3 (2×200 mL), saturated Na2S2O3 (2×200 mL) and water(2×200 mL), dried with MgSO4, and evaporated in vacuo. Recrystallization twice from ethanol (60 mL) yielded 5.35 g (91%) of the bromide as yellow needles. 1H NMR (300 MHz,CDCl3 delta ppm ): 9.83 (s, 1H), 4.36 (m, 4H); 13C NMR (75 MHz, CDCl3 delta ppm):179.0, 147.9,140.4, 118.8, 102.0, 65.5, 65.1.
  • 10
  • [ 75-75-2 ]
  • [ 204905-77-1 ]
  • polymer; monomer(s): 3,4-(ethylenedioxy)thiophene-2-carbaldehyde; methanesulfonic acid [ No CAS ]
  • 11
  • C6H5LiO2S [ No CAS ]
  • [ 93-61-8 ]
  • [ 204905-77-1 ]
  • 12
  • [ 204905-77-1 ]
  • [ 593231-56-2 ]
YieldReaction ConditionsOperation in experiment
98% With N-iodo-succinimide; toluene-4-sulfonic acid; In ethanol; at 25℃; for 0.166667h;Green chemistry; General procedure: The thiophene derivative (1 mmol, 1 equiv) was dissolved in EtOH (2mL) at the temperature indicated in Tables 1-5. Then, NIS (1 or 1.1 equiv, see Tables 1-5) was added followed by PTSA (10% mol). The mixture was stirred for 10 min, then sat. Na2S2O3 (2 mL) was added. The mixture was diluted with EtOAc (3 mL). After phase separation, the organic phase was washed with 1 M Na2CO3 solution, dried (MgSO4), filtered through cotton, and evaporated to give the iodinated thiophene derivative.
  • 13
  • [ 622-75-3 ]
  • [ 204905-77-1 ]
  • [ 368421-24-3 ]
  • 14
  • [ 1530-38-7 ]
  • [ 204905-77-1 ]
  • C15H14O3S [ No CAS ]
  • 15
  • [ 100-63-0 ]
  • [ 204905-77-1 ]
  • 3,4-ethylene-dioxythiophene-2-carbaldehyde-N-phenylhydrazone [ No CAS ]
  • 16
  • [ 204905-77-1 ]
  • C16H14O4S [ No CAS ]
  • 17
  • [ 204905-77-1 ]
  • 3-(5-(4-methoxystyryl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]
  • 19
  • [ 204905-77-1 ]
  • <i>N</i>,<i>N</i>'-bis-(7-thiophen-2-yl-2,3-dihydro-thieno[3,4-<i>b</i>][1,4]dioxin-5-ylmethylene)-cyclohexane-1,2-diamine [ No CAS ]
  • 20
  • [ 204905-77-1 ]
  • <i>N</i>,<i>N</i>'-bis-(7-thiophen-2-yl-2,3-dihydro-thieno[3,4-<i>b</i>][1,4]dioxin-5-ylmethyl)-cyclohexane-1,2-diamine [ No CAS ]
  • 21
  • [ 204905-77-1 ]
  • 3-(7-formyl-2,3-dihydro-thieno[3,4-<i>b</i>][1,4]dioxin-5-yl)-propionic acid methyl ester [ No CAS ]
  • 22
  • [ 204905-77-1 ]
  • 3-(5-formyl-3,4-ethylenedioxythiophen-2-yl)propionic acid [ No CAS ]
  • 23
  • [ 204905-77-1 ]
  • S-(5-formyl-3,4-ethylenedioxythiophen-2-yl)-3-thiopropionic acid [ No CAS ]
  • 24
  • [ 204905-77-1 ]
  • S-(5-formyl-3,4-ethylenedioxythiophen-2-yl)-1-thiohexane [ No CAS ]
  • 25
  • [ 204905-77-1 ]
  • S-(5-formyl-3,4-ethylenedioxythiophen-2-yl)-5-thiopentanoic acid [ No CAS ]
  • 26
  • [ 204905-77-1 ]
  • C19H21N3O3S [ No CAS ]
  • 27
  • [ 204905-77-1 ]
  • C26H26IN3O2S [ No CAS ]
  • 28
  • [ 204905-77-1 ]
  • [ 852054-44-5 ]
  • 29
  • [ 220260-66-2 ]
  • [ 204905-77-1 ]
  • N-methyl-2, 6-[1-(3,4-ethylenedioxythiophen-2-yl)ethen-2-yl]pyridinium triflate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% piperidine; In ethanol; for 3h;Heating / reflux; A solution of 3, [4-ETHYLENEDIOXYTHIOPHENE-2-CARBOXALDEHYDE] (0.456 g, 2.7 [MMOL)] in ethanol (10 ml) was added dropwise to a solution of 1,2, 6- trimethylpyridinium triflate (0.350 g, 1.3 mmol) and a few [ DROPS OF PIPERIDINE IN THE] same solvent (20 [ML).] Reaction mixture was [REFLUXED] for 3 hours and then cooled to 0 [C] giving the formation of a brown-yellow precipitate that was filtered under reduced pressure and crystallized from ethanol (0.539 g, 0.94 mmol, 72%). mp [103-105 C. 1H-NMR (DMSO-D6) 6] 8.24 [(1] H, t, J = 8.14), 8.16 (2 H, d, J = 8.09), 7.66 (2 H, d, J = 15. 54), 7.11 (2 H, d, J [= 15.] 63), 6.97 (2 H, s), 4.40 (4 H, m), 4.29 (4 H, m), 4.11 [(3] H, s) [; 13C-NMR (DMSO-D6)] 153.47 (2 C), 143.41 (2 C), 142.28 (1 C), 142.02 (2 C), 131.50 (2 C), 126.40 (2 C), 122.64 (2 C), 114.16 (2 C), 104.56 (2 C), 65. [27 (2] C), 64.30 (2 C), 41.16 (2 C). Anal [CALCD.] for [C23H2OF3NO7S3] : C, 47,99 %; H, 3.50 %; N, 2.43 %. Found: C, 47.90 %; H, 3.11 %; N, 2.20 %.
  • 30
  • [ 204905-77-1 ]
  • [ 859851-01-7 ]
YieldReaction ConditionsOperation in experiment
Under argon atmosphere, NaBH4 (0.40 g, 10.59 mmol) was added to a solution of EDOT-CHO (1.50 g, 8.82 mmol) in 92 mL of a mixture of CH2Cl2/ MeOH (1:1) and stirred at room temperature for 1h. The reaction was hydrolized with water and the aqueous phase extracted with chloroform. The organic phase was dried over MgSO4, and the solvent was removed under vacuum. Without further purification, the obtained alcohol (1.60 g, 9.3 mmol) was added over a mixture of triethylphosphate (2 mL/mmol) and iodine (2.36 g, 9.3 mmol). The reaction mixture was cooled at -20ºC and stirred for 2 hours and afterwards overnight at r.t. After removal of triethyl phosphate at reduced pressure, the crude was purified by column chromatography (silica gel, hexane:AcOEt, 1:1) giving 2.60 g of EDOT-phosphonate 3 as yellow oil (95% yield).
  • 31
  • [ 204905-77-1 ]
  • [ 354820-63-6 ]
  • [ 1058176-69-4 ]
  • 33
  • 1,1'-[(4,6-thieno[3,4-d]-1,3-dithiol-2-one-diyl)bismethylene]bis[triphenylphoshonium chloride] [ No CAS ]
  • [ 204905-77-1 ]
  • [ 1196714-98-3 ]
  • 34
  • [ 1049014-88-1 ]
  • [ 204905-77-1 ]
  • C28H25NO2S [ No CAS ]
  • 35
  • [ 1271-42-7 ]
  • [ 204905-77-1 ]
  • 3-(3,4-ethylenedioxythiophen-2-yl)-1-ferrocenyl-propenone [ No CAS ]
 

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